Acetic Acid → 5-(2,5-Dimethyl-1H-pyrrol-1-yl)-2-ethylpyridine

HRID 850108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 850108
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1)[CH3:2].[CH3:10][C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15].C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:15][C:14]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[N:4][CH:5]=2)[C:11]([CH3:10])=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 138607296-Ethylpyridin-3-amine

Produkt 1

HCID 193659555-(2,5-Dimethyl-1H-pyrrol-1-yl)-2-ethylpyridineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-ethylpyridin-5-amine (3.2 g, 26 mmol), 2,5-hexanedione (3.0 g, 26 mmol) and acetic acid (1 ml) in toluene (50 ml) was heated under reflux for 24 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane (50 ml) and water (20 ml). The aqueous phase was basified with aqueous sodium hydroxide (2M) and then extracted with dichloromethane (50 ml). The extract was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica by elution with dichloromethane/methanol (95:5) to give the title compound (2.38 g, 46%) as a colourless oil, which was characterised by 1H-N.M.R. spectroscopy.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between dichloromethane (50 ml) and water (20 ml)
  5. extractionextracted with dichloromethane (50 ml)
  6. dry with materialThe extract was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica by elution with dichloromethane/methanol (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-e580e35336ec4bcea097118f63c6beec
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06015825

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